Synthesis and Polymerization of Cationic bis(cyclopentadienyliron)arene Complexes Containing Arylazo Dyes

  • Alaa S. Abd-El-Aziz
  • Nelson M. Pereira
  • Waleed Boraie
  • Erin K. Todd
  • Tarek H. Afifi
  • Wes R. Budakowski
  • Ken J. Friesen

The synthesis of the title complexes was achieved via the reaction of \(\eta^{6}\)-p-dichlorobenzene- \(\eta^{5}\)-cyclopentadienyliron cations with 4,4′-bis(4-hydroxyphenyl)valeric acid to produce the diiron complexes which were then reacted with a number of arylazo dyes to give cationic bis(cyclopentadienyliron)arene complexes containing the arylazo dyes. These iron-containing monomers were subsequently polymerized via nucleophilic aromatic substitution using 1,8-octanedithiol, 4,4′-thiobisbenzenethiol, or bisphenol A to produce the desired coloured cationic organoiron polymers. The weight – average molecular weights were estimated to range from 11,800 to 31,600. UV–vis studies conducted in dimethylformamide (DMF) showed that the metallated polymers exhibited \(\lambda_{\max}\) of 412–491 nm. Addition of HCl to the polymer solution caused a bathochromic shift into the range of 515–530 nm. Thermogravimetric analysis (TGA) revealed that the iron moieties were cleaved between 205 and 248 °C while the polyether/thioether backbone degraded between 380 and 613 °C. Differential scanning calorimetry (DSC) showed that the polymers exhibited glass transition temperatures (Tg) ranging from 106 to 184°C.


Cyclopentadienyliron complexes organoiron polymers arylazo dyes nucleophilic aromatic substitution UV–vis studies thermal properties. 



Financial support provided by the Natural Sciences Engineering and Research Council of Canada (NSERC) and the University of Winnipeg are gratefully acknowledged.


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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • Alaa S. Abd-El-Aziz
    • 1
  • Nelson M. Pereira
    • 1
  • Waleed Boraie
    • 1
  • Erin K. Todd
    • 1
  • Tarek H. Afifi
    • 1
  • Wes R. Budakowski
    • 1
  • Ken J. Friesen
    • 1
  1. 1.Department of ChemistryThe University of WinnipegWinnipegCanada

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